When Bobi Wine was 26, he bought a brand-new Cadillac Escalade with spinning 24-inch rims. He was already a major star in Uganda, and the car, he says, was the first Escalade sold in all of East Africa. Wine’s music is a sunny blend of Jamaican dancehall and a local Afrobeat style called kidandali, but his persona back then was pure hip-hop. Local media reveled in tales of his trysts with various women and beefs with fellow stars.

One night, as Wine tells the story, he took his Escalade to a club in Kampala, the country’s capital, and was confronted by a man who bristled at the singer flaunting his wealth in a country consistently ranked as one of the poorest on Earth. The man approached the car, and slapped Wine across the face. Wine, a talented boxer, eagerly jumped from his SUV. Then the man drew a gun, put it to Wine’s head, and pummeled him mercilessly.

The man, Wine says, was a soldier who worked with Uganda’s head of military intelligence. In other words, well-connected and accountable to almost no one. At the time, Wine’s music leaned on party songs, love ballads, and braggadocio. He occasionally wrote about Uganda’s entrenched problems — poverty, sanitation, the AIDS epidemic — but generally turned a blind eye to the system enabling them. After all, he was thriving in it.

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Initially, Wine was aggrieved by this beatdown. But he was friends with generals, with businessmen, with politicians. He’d seen them inflict similar wrongs on others while he’d stood by and done nothing. The more he reflected on it, maybe he deserved it.

The incident redirected Wine onto the path where he stands now, at 38, a politician challenging the kind of injustice and impunity that slapped him in the face 12 years earlier. Wine, who was born Robert Kyagulanyi Ssentamu, won a seat in Uganda’s Parliament in 2017. Last year, he announced he’d run against the country’s 75-year-old autocrat Yoweri Museveni in early 2021 to become Uganda’s next president.

Museveni has been the country’s leader since 1986. His tenure has been marked by widespread government corruption and ruthless suppression of his political opposition. In the country’s last presidential contest, in 2016, his main challenger was arrested on election day.

Since Wine — who has been known as “the Ghetto President” for more than a decade — emerged as a challenger to Museveni, he has been prohibited from performing publicly. The government banned the red berets that are a trademark for supporters of Wine’s People Power movement. Wine has been arrested repeatedly and endured brutal treatment in government custody. In 2018, his driver was murdered in what some believe was an attempt to assassinate Wine, or at least serve him a dire warning. (A spokesman for the Ugandan government did not respond to a request to comment for this story.)

All this has only elevated Wine’s stature, not just in Uganda, but across Africa. Legendary South African pop star Yvonne Chaka Chaka called Wine “My Nelson Mandela in Uganda,” a comparison that, while slightly hyperbolic, is not totally off-base. People Power, which thus far is not aligned with a single party, has brought the young and the poor into the political arena. In a country where nearly 70 percent of the population is under 25 and poverty is the norm, Museveni has reason to be concerned.

“Museveni recognizes his government is corrupt and incompetent, and people are yearning for change,” says Daniel Kalinaki, general manager of editorial at the Nation Media Group and a political columnist at the Daily Monitor, Uganda’s largest independent newspaper. “He’s never faced someone like Bobi, who represents a real threat, a generational threat.”

On a Saturday morning in mid-December, rain pools outside the large, stately white house where Wine lives with his family, on the northern edge of Kampala. The first few times I knock on the door, there’s no response. After 15 minutes, he opens the door in a white terry-cloth bathrobe, rubbing sleep from his eyes.

“Oh, man, I’m so sorry,” he says, an embarrassed smile creeping from the corners of his mouth. “I just woke up.” He got in late last night from Zimbabwe, where he was performing. “Just give me five minutes to get ready.”

The house, which is surrounded by well-kept gardens, rows of banana trees, and a high cement wall, is quiet. Wine recently sent his wife and kids on vacation to a location he’d rather not reveal. “We’ve had some threats against my family,” he says.

Inside, the house is open, spacious, and relatively Spartan, save for a library just off the kitchen. There, family photos adorn one wall, not far from a small acoustic guitar and a hand drum. A nook contains reams of music and humanitarian awards. Bookshelves line another wall. On the top shelf is a soccer ball with an inscription commemorating the life of Thomas Sankara, the charismatic revolutionary, often known as “Africa’s Che Guevara,” who became president of Burkina Faso in 1983, then was assassinated four years later. Alongside it is a portrait of Haile Selassie, the Ethiopian emperor believed by Rastafarians to be God on Earth. Selassie was also, incidentally, assassinated.

Without his wife, Barbie, a social worker, at home, Wine is a little out of sorts. “I couldn’t find my shoes. I couldn’t find my socks,” he says as he emerges from his bedroom. He’s wearing a blue blazer, a black button-down, and black pants, along with, lo and behold, matching shoes and socks.

We pull out from the side gate of his property, and Wine, steering his white Toyota Land Cruiser down the thin, muddy road, begins playfully recounting his trip to Zimbabwe. “I sneaked into the country,” he says, whispering. “[Zimbabwean President] Mnangagwa wouldn’t want to see a troublemaker like me interacting with his opponents. I had to disguise myself. I felt like James Bond!”

Today, Wine is traveling with an assistant and two bodyguards. He’s got the surreal challenge of campaigning without being able to tell the public where he’s going to be. If he did, he says, “I’ll find the military and the police deployed there to beat anybody that shows up to say hello to me.” (The police have claimed that Wine’s meetings are unlawful.)

His demeanor turns serious. “They’re so scared of my interaction with the people. That explains why my concerts were banned. It explains why churches are cleared out when I show up. The regime is very scared of ordinary citizens. As much as they’re oppressing us, they’re very scared of us.” (In late March, Wine halted all People Power activities in response to the coronavirus pandemic, and released a catchy musical PSA.)

Wine performing in his younger days. Photograph courtesy of Bobi Wine

Courtesy of Bobi Wine

Wine’s first stop today doesn’t have any political significance: Basil’s Dental Clinic, to get a wisdom tooth pulled. “I want to go to my Christmas meals in better shape,” he jokes. As he walks toward the clinic, Eddy Mutwe, one of his bodyguards, laughs. “He’s still got that Kamwokya swagger,” he says. Wine is slender, with delicate features, and tends to walk with a distinct strut, taking long, graceful strides, his shoulders slightly hunched and his head tipped forward, perhaps the product, as Mutwe suggests, of his upbringing in Kamwokya, a Kampala slum.

After the dentist, Wine and his entourage head there, to a place they call “the barracks,” their de facto headquarters. There’s not much to it — a small office, a bathroom, a boxing heavy bag, and a dozen or so people milling around a dusty yard, all surrounded by an eight-foot wall — but Kamwokya itself is an important part of Wine’s story.

It’s the ghetto, but not just any ghetto. For those who care about Ugandan music, Kamwokya is Compton. Or Queensbridge. Descending a slope from the main road, a man hones a machete on a sharpening stone powered by an old bicycle. Small stalls line the road with locals selling green bananas, watermelons, pineapples, and beans. Goats and chickens amble around, unbothered. An army of boda bodas — the motorbike taxis that are the only effective way to navigate the city’s epic gridlock — zip up and down the street, their engines buzzing and spitting pungent plumes of exhaust into the air.

Wine grew up and began making music here. The walls of liquor stores, family restaurants, even a local police booth, are tagged with graffiti that reads, “Free Bobi,” “Free Bobi Concerts,” “People Power.”

A few buildings down from the barracks is a dirt road that leads to Dream Studios, built by Wine’s older brother, Eddy Yawe, in 2002. Yawe studied in Holland and the U.S., where he learned music production. He opened Dream at a time when the paucity of decent recording facilities in Uganda was leading prominent young artists like Bebe Cool and Jose Chameleone to uproot to Kenya. The place is basically just three soundproofed rooms and a large mixing desk, but in Kampala it was a revelation.

Wine was one of the first artists Yawe recorded here. Wine had sung with his brothers and sisters in church since he was a kid, but even as he got more serious about it, expectations were tempered. “Back then, music wasn’t making anyone money,” says Wine. “As a matter of fact, music was seen as a thing for failures. So initially I was involved in different little businesses, selling tapes and records, making bricks, doing this and that.”

As Wine’s songs gained traction locally, others noticed. “Most of the musicians turned around, and instead of going to Nairobi, they came here,” Yawe tells me. “Bobi and Bebe Cool formed a group.” They added others and christened themselves Fire Base Crew, which became, for a time, Ghetto Republic of Uganja.

This was the big bang of modern Ugandan pop. Throughout the 1990s, Congolese artists had been dominant on Ugandan radio and TV. In the early 2000s, that changed. “Bobi Wine, Bebe Cool, Jose Chameleone, these guys created the revolution in music,” says Douglas Lwanga, a music promoter and TV host. All three artists were big fans of dancehall stars like Buju Banton and Shabba Ranks, as well as South African reggae icon Lucky Dube, and injected their influence into the Ugandan mainstream.

In 2007, as Uganda prepared to host the Commonwealth Heads of Government Meeting, the regime swept vendors, beggars, and hustlers off Kampala’s streets in an effort to polish the city’s image. Wine took it personally. He hadn’t just been writing songs for and about these people; he felt he still was one. “You don’t displace your people to appease foreigners,” he says. “You don’t hide them away.” He released a song called “Ghetto,” which directly accused the government of betraying its citizens. Around this time, friends began calling Wine “the Ghetto President.”

Beside Dream Studios, down a narrow alleyway, is a cramped room where Wine lived as a young artist. A young boxer lives there now and he invites me in. The room has just enough space for a bed and desk, with a sheet hanging between them. Outside the room is an alcove, the back wall of which is dominated by a huge painting of the Rastafarian Lion of Judah, wearing a crown with the words “Fire Base” on it. Wine once identified as Rastafarian, but his beliefs are more fluid now. “I’ve been so many things,” he says. “Catholic, born-again Pentecostal Christian, Bahá’í, Rasta. I’m still all those things because I’ve got deep respect for them.”

Wine landed in Kamwokya by misfortune. He was born in 1982 during the Bush War. The conflict had begun one year earlier, when following a disputed election that put Milton Obote into power, a group of army officers, led by Museveni, initiated a guerrilla-style rebellion. Obote had already been Uganda’s president once before, during an increasingly unpopular stretch from 1966 to his overthrow by army general Idi Amin in 1971. Amin presided over a notoriously brutal military dictatorship until he too was ousted by force.

Before the Bush War, Wine’s family had been politically active and relatively well-to-do. “My family was an ally of Museveni,” says Wine. “My grandfather was killed in the Museveni liberation wars. His house was burned to the ground. My father was arrested by Obote’s regime, and sentenced to death. But thanks to the crazy corruption, my mother bailed him out.”

Wine’s father went into exile in Tanzania. A veterinarian by trade, he had three wives and at least 34 children — polygamy remains legal in Uganda to this day — but took only his first wife and some of his older children with him into exile. Wine’s mother, a nurse, moved Wine and several of his siblings to Kamwokya, where her father lived.

When the war ended, Museveni emerged as the country’s president and began immediately sidelining potential opposition in the name of national unity. Wine’s brother Steven was arrested for treason and ended up serving seven years. “My mother always told us the cause of our family’s predicament had been politics,” says Wine, “and always warned me we were better off staying out of politics.”

Nonetheless, it is, to some extent, the family business. During the 1996 election, Yawe released a song supporting Museveni’s opponent. He was arrested, he says, then beaten and tortured. “They tie a rope on your testicles, then [attach] a car battery and say, ‘Stand up.’ ” Yawe ran for an MP seat in 2011, which he says he lost due to “massive cheating,” and ran unsuccessfully in 2016 as well. He’s been arrested multiple times, but will run again in 2021.

One of Wine’s younger brothers, Mikie Wine, is considering running for the seat Wine himself would vacate if he became president. Both brothers recognize the personal peril they’re in as Wine’s campaign progresses. While Wine’s stature makes disappearing him risky, the death of one of his brothers would draw less attention. “I’d rather die fighting than die aimlessly,” Mikie tells me.

Wine largely resisted getting entangled in electoral politics until the past few years. The 2016 elections were a turning point. To build enthusiasm for his candidacy, Museveni recruited a host of top artists, including Cool and Chameleone — and paid them handsomely — to record a song called “Tubonga Nawe,” which translates as “We Are With You.” Wine says he rejected an offer of half a billion Ugandan shillings — about $135,000 — to participate. “He has always sided with the downtrodden, but that was a special moment,” says Yusuf Serunkuma, a doctoral fellow at Kampala’s Makerere Institute of Social Research and a political columnist for the weekly newspaper The Observer. “All his colleagues in the industry sided with the government. He singly chose not to.”

Museveni won the election, but something in Wine shifted: “After the 2016 elections, I realized nobody’s going to save us. We have to do it on our own. I knew it’d be much more effective if I didn’t only explain, I demonstrated. So I decided to run for office.” He shakes his head and laughs. “And, maaan, it opened a huuuge can of worms.”

Museveni has been Uganda’s leader since 1986. “[My] primary objective is to end the Museveni dictatorship,” Wine says. Photo credit: John Muchucha/AP/Shutterstock

John Muchucha/AP/Shutterstock

It doesn’t take much rain in Uganda to turn the country’s system of largely dirt roads into muddy waterways. Today’s floods will be responsible for at least five deaths in Kampala. In a rural area of the Mukono district, about an hour east, the rain has stopped, but some local men are barefoot, guiding cars and boda bodas through rushing reddish-brown waters. When the volunteers spot Wine in his Land Cruiser, they break into smiles and run toward the car.

“His Excellency!”

“Bobi!”

“People Power!”

They reach in and fist-bump with Wine. As the Land Cruiser pulls from the impromptu river, Wine turns to me. “That’s how it is when people are sure they’re not going to be beaten up or arrested for showing us love,” he says. Wine is on his way to what he calls “the last rites” for a friend’s father. The man, an influential figure in the community, died last week, and the event is like an Irish wake.

We arrive at a brightly colored house surrounded by multiple white tents. There’s a long buffet table, and about a hundred smartly dressed people sitting in white plastic chairs, eating. When Wine strides in, the place erupts. He shakes hands with several people at the head table, then the sound system begins playing one of his songs and a rush of bodies press close to greet him. When the hysteria settles, he climbs a small staircase and gives a speech, reminding everyone “not to forget why we’re here: to make this a better Uganda for the next generation.”

When he finishes, the sound system restarts, and he sings along to “Tuliyambala Engule,” a song he released that’s based on the traditional Christian hymn “When the Battle Is Over.” His version has lyrics about the country’s dysfunctional health system and a reminder for listeners to get their ID cards so they’re allowed to vote. This is as close as Wine gets to playing a concert in Uganda these days.

When Wine first ran for Parliament in 2017, Museveni’s NRM party poured money into the race in support of his opponent. Wine won in a landslide anyway. It didn’t take him long to grow disenchanted with Parliament. First, it rubber-stamped Museveni’s self-serving (and unpopular) effort to overturn the Constitution’s age limit for presidential candidates. When Wine was repeatedly blocked from performing, Parliament passed a resolution decreeing that he should be allowed to play. “But police said they don’t have to listen to Parliament,” he says. “It was then I knew Parliament was impotent.” He decided to run for president, but only as a way of achieving a larger goal. “The primary objective is to end the Museveni dictatorship, return the rule of law, make sure the independence of the three arms of government is observed.”

Uganda, a landlocked country of roughly 45 million people, is still a young nation. It was a British colony until 1962, and like many former colonies, its borders were somewhat haphazardly drawn to include kingdoms, tribes, clans, and ethnic groups that didn’t necessarily share much history or culture. English is the official language, but more than 40 other languages are more commonly spoken in their regions.

Undergirding much of modern Ugandan history is a tug-of-war between groups vying for power and money. A significant strain of opposition against Museveni is based on the belief that his regime is, as Kalinaki puts it, “a small, ethnic cabal,” that has heaped favor on his own Banyankole people from western Uganda — and particularly his Bahima subtribe — at the expense of the rest of the country. Wine’s ethnic group, the Baganda, is the country’s largest, but has rarely been politically dominant.

Wine has been arrested more than 20 times since he ran for Parliament, according to his lawyer, but one incident stands out. On August 13th, 2018, both Wine and Museveni were campaigning in the northwestern city of Arua in support of opposing candidates in a parliamentary by-election. The government claims Museveni’s motorcade was pelted with rocks, leading to altercations between police and protesters. In the ensuing chaos, Wine’s driver was shot and killed. Wine says he retreated to a hotel where he was eventually discovered by soldiers who knocked down his door with an iron bar, then beat him with it.

According to Wine, he was bundled into a vehicle, where the abuse persisted. “They squeezed my testicles,” he recounted weeks later. “They started hitting my ankles with pistol butts. … They used something like pliers to pull my ears. … Then they hit my back and continued to hit my genitals.” Eventually, he says, he was bashed in the head and lost consciousness. At least 34 others were arrested, and many were abused, including the opposition candidate who won the election. Wine was charged with possession of a firearm, a charge that was quickly dropped. Then he was re-arrested and charged with treason. After being detained for nearly two weeks, he was released. When I ask him about the incident, his face falls.

“It’s a very bad memory,” he says quietly. The brutality left lasting scars. “They broke my skull here,” he says, pointing to a spot over his eye. “Every once in a while, it swells by itself. My back has never completely healed. Psychologically, I don’t think it will ever go away.” The episode was clarifying. “It educated me on how low this regime is willing to sink to remain in power.”

The incident was international news. In an open letter, artists like Chris Martin, Peter Gabriel, and Damon Albarn condemned Wine’s treatment. The attention has been a double-edged sword. While the higher profile has provided some protection for Wine and publicity for People Power, it has also edged an earnest movement close to a cult of personality. At the barracks in Kamwokya, Wine meets a man named Emma, who had traveled 10 hours to beseech him to visit his hometown to build support for People Power. Wine is polite, and offers to send others in his place who “will say the same things I say,” but he’s a little exasperated.

Wine knows he’s not the only one suffering persecution. Kizza Besigye has stood against Museveni in the past four elections at great personal cost: He’s been repeatedly jailed, charged with rape and treason, and for a time, forced into exile. He plans to run again in 2021. Ziggy Wyne, another member of Wine’s Fire Base Crew, was allegedly tortured to death by authorities in August (the government claimed he died in a motorcycle accident). At a press conference in March, Wine detailed the death or disappearance of 10 other People Power supporters and the imprisonment of dozens more.

At least a half-dozen other artists have announced intentions to run for office, allied with Wine and People Power. “Music in Uganda has become another parliament,” says Dr. Hilderman, a dancehall artist running for Parliament. “People expect MPs to represent their views. When they fail to do so, they turn to us as their ambassadors. The people are encouraging us to air out their views, to talk about what they’re going through.”

During a concert last September, Ronald Mayinja, a pioneer of politically conscious music in Uganda who is also contesting a parliamentary seat, sang a song criticizing Museveni while Museveni was in the audience. In recent months, both Hilderman and Mayinja have found promoters unwilling to book their shows. Mayinja tells me he has also gotten threatening phone calls. “Even when you called me, I was suspicious,” he says. “I was like, ‘It could be a trap.’ They see we’re telling the youth the truth. They don’t want anyone to talk about these things.”

Cynical observers see the increasing politicization of music as a career move. “Fact is, music is not profitable,” says Lwanga. “So when people saw the success Bobi had, he inspired a whole string of artists to join that direction.”

Bebe Cool, a staunch ally and friend of Museveni’s for decades, is among the cynics. He expects most musicians running for office will get trounced. “One, they lack budgets,” he says. “Two, they’re not as educated. Three, when you see crowds, it doesn’t mean they transform into votes.”

Jose Chameleone is running for mayor of Kampala. He’s heard these criticisms, but he’s anxious to convince me — and others — of the sincerity of his campaign. “I’m not going to become famous being mayor of Kampala,” he says. “I’m not going to fly business class being mayor. I’ve done that. I want to contribute my legacy to the people denied a chance.”

Dennis Tumuhairwe, a leader of the Uganda Young Democrats and Wine’s former political assistant, believes the music community will prove a decisive force. “Having major artists join the opposition to take Museveni down seems like a done deal for Museveni,” he says. “We think we’re starting a revolution we’re going to win.”

Wine was arrested on his way to a press conference to announce a show cancellation. Photo credit: Badru Katumba/AFP/Getty Images

Badru Katumba/AFP/Getty Images

Bobi Wine is almost certainly going to lose the election in 2021. That’s if he’s even allowed on the ballot — and alive to see it. Despite the semblance of democratic norms, Uganda is nothing resembling a functioning democracy. “Museveni controls everything,” says Serunkuma. “He appoints the judges. Most of the senior generals come from his area. In 2017, he had the military move into the Parliament and beat up MPs.”

Serunkuma describes Museveni’s regime as a constitutional autocracy. “The autocrats of today operate like ghosts,” he says. “They give you a facade that looks functional. Museveni doesn’t rig an election with obnoxious margins. He’s really smart.” In each of Museveni’s five elections, he’s collected between 59 percent and 75 percent of the vote. “He’s very keen not to be seen as Obote or Amin,” says Kalinaki. “It’s important to him that there’s some veneer of legitimacy.”

Museveni has also worked to make himself seem indispensable to the West. He has been a reliable partner in the fight against terrorism throughout and beyond East Africa. Ugandan troops were part of George W. Bush’s “coalition of the willing,” and have been deployed as part of anti-terrorism and peacekeeping operations in Iraq, Afghanistan, and Somalia. The U.S. rewards Museveni with nearly $1 billion in development and security assistance every year.

Museveni has further endeared himself to the West by opening Uganda’s borders to the African refugees most of Europe is shutting out. As of late 2018, Uganda had roughly 1.5 million refugees living in the country, and had taken in more than $200 million in humanitarian assistance to help settle them in 2018 alone. All this makes it that much easier to overlook Museveni’s abysmal human-rights record.

Wine makes the point that fighting terrorism is in his nation’s best interest, but “our partners in the fight shouldn’t be Museveni’s partners, they should be Uganda’s partners. They shouldn’t work with any individual, they should work with the institutions.” Wine’s politics are unapologetically populist — he’s walked back his previous support for Uganda’s repugnant Anti-Homosexuality Act, which was signed into law in 2014, then subsequently ruled unconstitutional amid international outcry — but he’s no demagogue. He promises to restore presidential age and term limits. He’d even like to offer Museveni amnesty after the election, though he admits that may depend on what happens between now and then. “We want to end this vicious circle of leaders that leave power and have to live in exile.”

There are no reliable polls measuring support for Wine, Museveni, or any other presidential candidates. Some point to the size of the crowds Wine attracts as evidence of broad backing. Others question whether he has the logistical know-how to get out his supporters, many of whom are young and may not have voted in the past. Wine told me he believes he’d beat Museveni with 80 to 90 percent of the vote in a fair election, though that seems hyperbolic. The conventional wisdom is that Museveni remains popular with rural voters, who make up a majority of the population. All these projections are little better than guesswork.

The election won’t be free or fair. There have been consistent charges of ballot-stuffing, bribery, and voter intimidation in the past, and few I spoke to expect anything different in 2021. “I don’t think anyone can beat Museveni in the current setting,” says Kalinaki. “It’s very difficult to mobilize against the state. Even if Jesus Christ ran against Museveni, he’d lose.”

Even if Wine wins more votes, the idea of Museveni graciously stepping aside seems nothing short of a fantasy, even to Wine himself. “Of course, it’s very unlikely because Museveni has personalized everything, made everybody feel that Museveni is the state and the state is him,” says Wine. “He’s bent on shrinking the political space, to the extent of wanting to take the lives of his opponents. But if it’s clear we won, he’ll be left with no choice. The people of Uganda will rise up against Museveni. They’ll say, ‘Enough!’ ”

Museveni seems intent on countering the threat Wine and his fellow artists pose. This past fall, he appointed several prominent musicians as new presidential advisers. Catherine Kusasira, a popular kidandali singer who frequently performs in a band alongside Mayinja, was tapped as a new presidential adviser for Kampala Affairs; Buchaman, a dreadlocked Rastafarian who’d once been vice president of Wine’s Fire Base Crew, became Museveni’s Special Envoy for Ghetto Affairs; Full Figure, a brash singer who’d been a People Power supporter, was named a Presidential Adviser. While many dismissed these appointments as a cynical ploy to buy credibility among Uganda’s young and poor, that doesn’t mean it might not work.

One sunny afternoon, I trail Buchaman in a two-car convoy to Kasokoso, a Kampala slum that sits alongside a landfill. Buchaman is short, and walks with a crutch to compensate for a left leg that, he tells me, was hit by a bullet when he was a child during the Bush War, but which Ugandan media have reported was crippled by a childhood bout with polio. His musical association with Wine makes him a celebrity in places like this, and when he gets out of the car, he’s swarmed. He marches surprisingly swiftly through the muddy streets, intermittently shouting things like “Ghetto power!” or miming the sound of a gun firing in the air, “Pop! Pop! Pop!” attracting more bystanders as he moves. The growing caravan squeezes between corrugated-tin fruit stalls and rough-clapboard shacks, settling briefly in a tiny courtyard where Buchaman speaks to the assembled throngs, before marching deeper into the ghetto. We arrive at the grassy front yard of a house, where several chairs and a bench have been arranged beneath two trees. For the next hour, Buchaman and his team sit there, holding court. One by one, local residents parade before him, asking for help to build a local health center, to send money for schools, for job training, to fix the roads, to combat crime.

Buchaman is here representing the government, but when I ask about it, he doesn’t exactly embrace Museveni and the NRM. “I’ve not been a supporter,” he says. “Even now, why I am behind Museveni is to help the ghetto people. I’m not part of any political party.” He repeats something I heard when I met with Catherine Kusasira, another singer-turned-government-envoy: The problem isn’t that Museveni is corrupt or incompetent, but that the local politicians he’s worked with are. “He has been giving money to the wrong people, to ministers and MPs, and they do nothing for the ghetto,” Buchaman says. “They’ve been eating the money.” He believes he can do better: “I know what pains the ghetto people.”

The whole afternoon feels performative, but people here seem genuinely happy that someone at least bothered to come listen to them. And this is the point. Museveni doesn’t necessarily need them to vote for him. He doesn’t even need them not to vote for Wine. He just needs to give them something to think about. He may even address some of their complaints. “There’s going to be lots of money poured into the ghetto,” says Kalinaki. “The intention isn’t to cure the long-standing problems but to create lag time between the election outcome and people going back to their miserable lives. If you throw money at the problem, it’s a bit like bank robbers throwing bank notes in the air.”

The goal is to avoid the one thing that can actually force Museveni from office: a full-scale, Arab Spring-style uprising by the country’s young and impoverished. “That’s the only threat Bobi Wine presents Museveni,” says Serunkuma. “It’s not an electoral threat. It’s a threat to mobilize bodies onto the streets of Kampala.”

Indeed, in the past decade, street protests have ousted a series of entrenched African dictators, first in Tunisia and Egypt, then in Burkina Faso, the Democratic Republic of Congo, Zimbabwe, Algeria, and Sudan. This is essentially what Wine’s campaign is about: creating momentum and setting the conditions to spark a revolution. But it’s a serious gamble. “We’re in the middle of a fight,” Wine says. “Museveni believes in violent fight. We believe in logic, and psychological and democratic fight. We know he won’t go without a fight. But we’re over 40 million people. We know Gaddafi, Bouteflika, and Omar al-Bashir wouldn’t go without a fight. But they went.”

He and his backers are counting on protesters not just going into the streets, but also staying there once bullets start flying. Not everyone thinks they will. Several people I spoke to who are broadly supportive of democratic change just don’t think Uganda’s impoverished youth have the stomach for the fight. “People like Bobi underestimate what the sound of gunfire does to people who in many cases have never seen war,” says Kalinaki. “That generation doesn’t know what a Katyusha [rocket launcher] sounds like.”

Older Ugandans with memories of the Bush War and the pre-Museveni days may be desperate to avoid returning to that instability. “I was here during the bad days, when there were a lot of killings and lootings,” says Edward Ssendikaddiwa, a music critic and panelist on Dembe FM in Kampala. “There was a time when soldiers would break into our house when we were inside, and take whatever they can — to the extent that my dad would shout, ‘Please, don’t break! Let me open for you!’ because he was tired of repairing the same window they’d break. Having seen that, all I have to say is, whatever happens in 2021, I prefer peace.”

That attitude becomes a de facto vote for Museveni, even for someone outwardly opposed to his regime. The stakes have been raised to the point where Wine doesn’t just have to convince people to support the cause, he must convince a significant number to be willing to die for it. “The majority have nothing to lose,” he says. “A life that can be taken by police or any security operative, that’s no life. A life that can be taken by being taken to a hospital that has no drugs is worthless. These lives that we have, we know they’re worthless.”

Wine himself has plenty to lose. Music has made him wealthy, though his inability to play shows here for the past two years has taken a bite from that wealth. “I can no longer enjoy the things I used to enjoy,” he says. “Ordinarily, every weekend, I’d have concerts and be making a lot of money. I’d be driving the latest cars. I’d have spending cash of maybe 100 million [Ugandan shillings],” or about $27,000.

He’s still doing OK. On my final full day in Uganda, I meet him at One Love Beach, a six-acre plot of rolling green lawns, palm trees, and beachfront on the shore of Lake Victoria, south of Kampala’s city center. He bought the property 15 years ago with the intention of building a house and retiring to it when he turned 35. Instead, he opened the beach — and himself — to the public. For less than a dollar you can spend the day here, swimming, barbecuing, playing soccer and volleyball, or dancing to the throb of Afro-beat pouring from the sound system.

Today is Sunday, and Wine looks dressed for retirement: blue, floral-print, short-sleeve button-down and matching shorts, with dark leggings underneath, along with blue high-tops. “Man, I miss this place,” he tells me, waving a hand toward the beach. He used to come every week, but this is his first visit in nearly three months. He’s invited friends, and has goat, chicken, and fish sizzling on a grill within a grove of trees.

His manner today is more subdued than the day before. There’s no sense he regrets the mantle he’s taken up, but he clearly misses some of what he left behind. “Every once in a while, I’d love to drink, be tipsy and happy, and dance with my friends,” he says. “But I can’t because I represent something greater than me.” I tell him he sounds like someone reconsidering that retirement. He laughs. “The question is, ‘Do I ever think I should just retire?’ ” He smiles. “All the time.”

Wine still records when he can, but even his music now must fit within narrower parameters. Anything breezy and carefree is unlikely to see the light of day. “People expect more revolutionary music from me,” he says.

The next year is going to be a tumultuous one — for him, for People Power, for Uganda itself. In a few weeks, he’ll be arrested as he tries to meet with supporters. Police will fire tear gas and bullets to disperse the crowds. (The police claimed Wine had been permitted to have an assembly indoors but not outdoors.) He and other People Power leaders will be held in a crowded cell for most of a day. The government will continue to block his efforts to meet with voters.

He knows he has worse in store. Multiple criminal charges hang over his head, including the treason charge and another for inciting violence. When I ask what he’ll do if the government convicts him, locks him up, and declares him ineligible to run for president, he stares at me grim-faced for a long beat. “We shall cross that bridge when we get to it,” he says, then smiles widely. “I mean, what can I say?”

Throwing Wine in prison forever, killing him, or unleashing a violent crackdown against his supporters, would engender criticism from the international community, but that’s probably not what’s stopping Museveni and his regime from doing those things. What is keeping them in check is the fear of triggering the exact sort of revolutionary spark that Wine is hoping to generate. What exactly might trigger that neither side knows. So they grope in the dark toward a line in the sand that may or may not even exist.

Serunkuma struggles to see how this all ends well for Wine. “Bobi is in a very difficult position,” he says. “He’s like a tragic hero caught up in this.” Success for Wine may involve reorienting his goals. “The best thing Bobi can do is to make a better connection between people’s welfare and the political choices they make,” says Kalinaki. “If he can build that among young people, then even if he doesn’t dislodge Museveni in 2021, or even in 2026, he’ll have brought some political consciousness to a generation that, when it’s in its thirties or forties, will make the painful decisions necessary not just to get rid of Museveni but to get rid of Musevenism.”

That’s not the end Wine wants, but even if his mission fails, if he ends up in prison or dead and Museveni’s still in power, he’s comfortable with his decisions. “Everything is worth it,” he says. “Already, the awakening people have received is worth it.” He’s looking out past his beach at the late-afternoon sun reflecting off Lake Victoria. His voice gets quiet. “There are some causes so noble that even a mere attempt is noble enough.”